Novel boron compound and organic light-emitting diode comprising same

Abstract

The present disclosure relates to a boron compound useful in an organic light-emitting diode and an organic light-emitting diode comprising same and, more particularly, to a boron compound represented by any one of [Chemical Formula A] to [Chemical Formula E], wherein [Chemical Formula A] to [Chemical Formula E] is as defined in the description.

1 . A boron compound represented by any one of the following Chemical Formulas A to E: 
       
         
           
           
               
               
           
         
         wherein, 
         X 1  is O, S, or NR 1 , 
         X 2  is O, S, or NR 2 , 
         Y 1  is any one selected from O, S, Se, NR 3 , and CR 4 R 5 , 
         Y 2  is any one selected from O, S, Se, NR 6 , and CR 7 R 8 , 
         Q 1  and Q 2 , which may be same or different, are each independently a substituted or unsubstituted aromatic hydrocarbon ring of 6 to 50 carbon atoms, or a substituted or unsubstituted heteroaromatic ring of 2 to 50 carbon atoms, 
         the Q1 ring moiety having no amine radicals as substituents or including one amine radical represented by —NR 9 R 10  as one substituent thereon, 
         the Q2 ring moiety having no amine radicals as substituents thereon or including one amine radical represented by —NR 11 R 12  as a substituent thereon, 
         R 1  to R 8 , which may be same or different, are each independently any one selected from a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl of 1 to 30 carbon atoms, a substituted or unsubstituted aryl of 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl of 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryl of 2 to 50 carbon atoms, a substituted or unsubstituted alkoxy of 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy of 6 to 30 carbon atoms, a substituted or unsubstituted alkylthio of 1 to 30 carbon atoms, a substituted or unsubstituted arylthio of 5 to 30 carbon atoms, a substituted or unsubstituted alkylamine of 1 to 30 carbon atoms, a substituted or unsubstituted arylamine of 5 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl of 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl of 5 to 30 carbon atoms, a nitro, a cyano, and a halogen, 
         R 9  to R 12 , which may be same or different, are each independently selected from a Hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl of 1 to 30 carbon atoms, a substituted or unsubstituted aryl of 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl of 3 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl of 2 to 50 carbon atoms, 
         R 9  and R 10  may be bonded to each other to additionally form an aliphatic or aromatic mono- or polycyclic ring, and R 11  and R 12  may be bonded to each other to additionally form an aliphatic or aromatic mono- or polycyclic ring, 
         R 3  to R 5  and R 6  to R 8  may each independently bonded to the Q1 ring moiety to additionally form an aliphatic or aromatic mono- or polycyclic ring, 
         R 4  and R 5  may be boned to each other to additionally form an aliphatic or aromatic mono- or polycyclic ring, 
         R 7  and R 8  may be bonded to each other to additionally an aliphatic or aromatic mono- or polycyclic ring, 
         the ring accounted for by Cy1 includes a substituted or unsubstituted alkylene of 1 to 10 carbon atoms as a ring constituent except for the two carbon atoms as ring members of the unsaturated pentagonal ring bearing X 1 , 
         the ring accounted for by Cy2 includes a substituted or unsubstituted alkylene of 1 to 10 carbon atoms as a ring constituent except for the two carbon atoms as ring members of the unsaturated pentagonal ring bearing X 2 , and 
         R 6  to R 8  in Chemical Formulas A and Chemical Formula B may be bonded to the Q2 ring moiety to additionally form an aliphatic or aromatic mono- or polycyclic ring, 
         wherein, the term “substituted” in the expression “substituted or unsubstituted” used for the compound of Chemical Formulas A to E means having at least one substituent selected from the group consisting of a deuterium atom, a cyano, a halogen, a hydroxy, a thiol, a nitro, an alkyl of 1 to 24 carbon atoms, a halogenated alkyl of 1 to 24 carbon atoms, an alkenyl of 2 to 24 carbon atoms, an alkynyl of 2 to 24 carbon atoms, a heteroalkyl of 1 to 24 carbon atoms, an aryl of 6 to 24 carbon atoms, an arylalkyl of 7 to 24 carbon atoms, an alkylaryl of 7 to 24 carbon atoms, a heteroaryl of 2 to 24 carbon atoms, a heteroarylalkyl of 2 to 24 carbon atoms, an alkoxy of 1 to 24 carbon atoms, an alkylamino of 1 to 24 carbon atoms, a diarylamino of 12 to 24 carbon atoms, a diheteroarylamino of 2 to 24 carbon atoms, an aryl(heteroaryl)amino of 7 to 24 carbon atoms, an alkylsilyl of 1 to 24 carbon atoms, an arylsilyl of 6 to 24 carbon atoms, an aryloxy of 6 to 24 carbon atoms, and an arylthionyl of 6 to 24 carbon atoms. 
       
     
     
         2 . The boron compound of  claim 1 , wherein Y 1  is N—R 3  or Y 2  is N—R 6  in Chemical Formulas A to E, R 3  and R 6  being defined as in  claim 1 . 
     
     
         3 . The boron compound of  claim 2 , wherein Y 1  is N—R 3  and Y 2  is N—R 6 . 
     
     
         4 . The boron compound of  claim 2 , wherein R 3  and R 6  are same or different and are each independently a substituted or unsubstituted aryl of 6 to 50 carbon atoms or a substituted or unsubstituted heteroaryl of 2 to 50 carbon atoms. 
     
     
         5 . The boron compound of  claim 4 , wherein R 3  and R 6  are same or different and each independently selected from a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted anthracenyl, a substituted or unsubstituted phenanthrenyl, and a substituted or unsubstituted fluorenyl and any one of R 3  and R 6  can bond to the Q1 or Q2 ring moiety to form a mono- or polycyclic ring. 
     
     
         6 . The boron compound of  claim 1 , wherein at least one of Y 1  and Y 2  in Chemical Formulas A to E is an oxygen atom (O) or sulfur atom (S). 
     
     
         7 . The boron compound of  claim 1 , wherein Q1 and Q2 are same or different and are each independently a substituted or unsubstituted aromatic hydrocarbon ring of 6 to 18 carbon atoms or a substituted or unsubstituted heteroaromatic ring of 2 to 18 carbon atoms. 
     
     
         8 . The boron compound of  claim 7 , wherein the aromatic hydrocarbon ring of Q2 in Chemical Formulas A and B is any one selected from Structural Formulas 10 to 21, below: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         wherein, “-*” denotes bonding sites at which the corresponding carbons in the aromatic ring of Q2 bond to the boron atom and the linker Y 2 , respectively, and 
         R's, which may be same or different, are each independently any one selected from a hydrogen atoms, a deuterium atom, a cyano, a halogen, a hydroxy, a nitro, an alkyl of 1 to 24 carbon atoms, a halogenated alkyl of 1 to 24 carbon atoms, a cycloalkyl of 3 to 24 carbon atoms, an alkenyl of 2 to 24 carbon atoms, an alkynyl of 2 to 24 carbon atoms, a heteroalkyl of 1 to 24 carbon atoms, an aryl of 6 to 24 carbon atoms, an arylalkyl of 7 to 24 carbon atoms, an akylaryl of 7 to 24 carbon atoms, heteroaryl of 2 to 50 carbon atoms, a heteroarylalkyl of 2 to 24 carbon atoms, an alkoxy of 1 to 24 carbon atoms, an alkylamino of 1 to 24 carbon atoms, a diarylamino of 12 to 24 carbon atoms, a diheteroarylamino of 2 to 24 carbon atoms, an aryl(heteroaryl)amino of 7 to 24 carbon atoms, an alkylsilyl of 1 to 24 carbon atoms, an arylsilyl of 6 to 24 carbon atoms, an aryloxy of 6 to 24 carbon atoms, and an arylthionyl of 6 to 24 carbon atoms, and 
         m is an integer of 1 to 8 wherein when m is 2 or more or two or more R's is present, the corresponding R's may be same or different. 
       
     
     
         9 . The boron compound of  claim 7 , wherein the aromatic hydrocarbon ring of Q1 in Chemical Formulas A to E is a ring represented by the following Structural Formula B: 
       
         
           
           
               
               
           
         
         wherein “-*” denotes bonding sites at which the corresponding carbons in the aromatic ring of Q1 bond to the boron atom (B) and the linkers Y 1  and Y 2 , respectively, and 
         R 55  to R 57 , which may be same or different, are each independently any one selected from a hydrogen atom, a deuterium atom, a cyano, a halogen, a hydroxy, a nitro, an alkyl of 1 to 24 carbon atoms, a halogenated alkyl of 1 to 24 carbon atoms, a cycloalkyl of 3 to 24 carbon atoms, an alkenyl of 2 to 24 carbon atoms, an alkynyl of 2 to 24 carbon atoms, a heteroalkyl of 1 to 24 carbon atoms, an aryl of 6 to 24 carbon atoms, an arylalkyl of 7 to 24 carbon atoms, an akylaryl of 7 to 24 carbon atoms, a heteroaryl of 2 to 50 carbon atoms, a heteroarylalkyl of 2 to 24 carbon atoms, an alkoxy of 1 to 24 carbon atoms, an alkylamino of 1 to 24 carbon atoms, a diarylamino of 12 to 24 carbon atoms, a diheteroarylamino of 2 to 24 carbon atoms, an aryl(heteroaryl)amino of 7 to 24 carbon atoms, an alkylsilyl of 1 to 24 carbon atoms, an arylsilyl of 6 to 24 carbon atoms, an aryloxy of 6 to 24 carbon atoms, and an arylthionyl of 6 to 24 carbon atoms, and 
         any adjacent two of R 55  to R 57  may be linked to each to each other to form an additional mono- or polycyclic aliphatic or aromatic ring. 
       
     
     
         10 . The boron compound of  claim 1 , wherein
 the ring accounted for by Cy1 in Chemical Formulas A to E includes as a ring constituent a linker represented by the following Structural Formula D:   
       
         
           
           
               
               
           
         
         the ring accounted for by Cy2 in Chemical Formulas C to E includes as a ring constituent a linker represented by the following Structural Formula E: 
       
       
         
           
           
               
               
           
         
         wherein “-*” denotes a bonding site to two adjacent carbon atoms within the unsaturated pentagonal ring bearing X 1  or X 2  as a ring member, and 
         Z and Z′, which are same or different, are each independently any one selected from a single bond, —C(R 69 )(R 70 )—, and —C(R 71 )(R 72 )—C(R 73 )(R 74 )—, 
         wherein R 61  to R 74 , which may be same or different, are each independently selected from a hydrogen atom, a deuterium atom, a halogen, a substituted or unsubstituted alkyl of 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl of 3 to 20 carbon atoms, a substituted or unsubstituted aryl of 6 to 20 carbon atoms, a substituted or unsubstituted heteroaryl of 2 to 20 carbon atoms, a substituted or unsubstituted alkylsilyl of 1 to 20 carbon atoms, and a substituted or unsubstituted arylsilyl of 6 to 20 carbon atoms wherein the term ‘substituted” in the expression “substituted or unsubstituted” used is as defined above. 
       
     
     
         11 . The boron compound of  claim 1 , wherein the Q1 ring moiety has no amine radicals as substituents thereon and only the Q2 ring moiety includes one amine radical represented by —NR 11 R 12  as a substituent thereon in Chemical Formulas A to E. 
     
     
         12 . The boron compound of  claim 1 , wherein the amine radicals represented by —NR 9 R 10  as a substituent on the Q1 ring moiety or the amino radicals represented by —NR 11 R 12  as a substituent on the Q2 ring moiety in Chemical Formulas A to E are same or different and are each independently an amine represented by the following Structural Formula F: 
       
         
           
           
               
               
           
         
         wherein “-*” denotes a bonding site to a carbon atom as a member in the aromatic ring of at least one of Q1 and Q2, and 
         Ar 11  and Ar 12 , which are same or different, are each independently a substituted or unsubstituted aryl of 6 to 18 carbon atoms. 
       
     
     
         13 . The boron compound of  claim 1 , wherein the boron compound is any one selected from <Compound 1> to <Compound 243> 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
     
     
         14 . An organic light-emitting diode, comprising:
 a first electrode;   a second electrode facing the second electrode; and   an organic layer interposed between the first electrode and the second electrode, wherein the organic layer includes a boron compound of  claim 1 .   
     
     
         15 . The organic light-emitting diode of  claim 14 , wherein the organic layer comprises at least one of a hole injection layer, a hole transport layer, a functional layer capable of both hole injection and hole transport, an electron blocking layer, a light-emitting layer, an electron transport layer, an electron injection layer, and a capping layer. 
     
     
         16 . The organic light-emitting diode of  claim 14 , wherein the organic layer disposed between the first electrode and the second electrode includes a light-emitting layer composed of a host and a dopant, the boron compound represented by any one of Chemical Formulas A to E servings as the dopant. 
     
     
         17 . The organic light-emitting diode of  claim 16 , wherein the light-emitting layer uses an anthracene derivative represented by the following Chemical Formula F as the host: 
       
         
           
           
               
               
           
         
         wherein, 
         R 21  to R 28 , which are same or different, are each as defined for R 1  to R 8  in  claim 1 ; 
         Ar 9  and Ar 10 , which are same or different, are each independently any one selected from a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl of 1 to 30 carbon atoms, a substituted or unsubstituted aryl of 6 to 50 carbon atoms, a substituted or unsubstituted alkenyl of 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl 2 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl of 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl 5 to 30 carbon atoms, a substituted or unsubstituted heteroaryl of 2 to 50 carbon atoms, a substituted or unsubstituted heterocycloalkyl of 2 to 30 carbon atoms, a substituted or unsubstituted alkoxy of 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy of 6 to 30 carbon atoms, a substituted or unsubstituted alkylthio of 1 to 30 carbon atoms, a substituted or unsubstituted arylthioxy of 6 to 30 carbon atoms, a substituted or unsubstituted alkylamine of 1 to 30 carbon atoms, a diarylamino of 12 to 24 carbon atoms, a diheteroarylamino of 2 to 24 carbon atoms, an aryl(heteroaryl)amino of 7 to 24 carbon atoms, a substituted or unsubstituted alkylsilyl of 1 to 30 carbon atoms, and a substituted or unsubstituted arylsilyl of 6 to 30 carbon atoms; 
         L 13 , which functions as a linker, is a single bond or is selected from a substituted or unsubstituted arylene of 6 to 20 carbon atoms, and a substituted or unsubstituted heteroarylene of 2 to 20 carbon atoms; and 
         k is an integer of 1 to 3, wherein when k is 2 or greater, the corresponding L 13 's are same or different. 
       
     
     
         18 . The organic light-emitting diode of  claim 15 , wherein at least one selected from among the layers is deposited using a single-molecule deposition process or a solution process. 
     
     
         19 . The organic light-emitting diode of  claim 14 , wherein the organic light-emitting diode is used for a device selected from among a flat display device; a flexible display device; a monochrome or grayscale flat illumination; and a monochrome or grayscale flexible illumination.